Actually the Gemara mentions three separate Yeshus.
1. A certain Yeshu ben Pandera (Sanhedrin 67a and Avoda Zara 17a) was the son of Mary Magdalene (Miriam Magdalei Neshaya – Miriam the Women’s Hairstylist). He is apparently the source of the nickname Yushka Pundrick. As she was the wife of Pappus ben Yehuda (Gittin 90a) this Yeshu must have lived around the time of the Bar Kochba rebellion (see Berachot 61b) – a century after Pilate.
2. There was also a Yeshu haNotzri who was a talmid of Yehoshua ben Perachia and fled with him when Yannai was slaughtering the chachamim (Sanhedrin 107b). This was over a century before Pilate.
As for maintaining good relations with your family you might want to read “After the Return” by Rabbi Mordechai Becher (full disclosure: I did not read the book so I cannot comment on its content).
3. Yaakov the Heretic quoted Yeshu to Rabbi Eliezer (Avodah Zarah, 16b-17a). As Rabbi Eleizer lived around the time of the Churban this Yeshu could have lived during the time of Pilate assuming that Yaakov the Heretic was already an elderly man when he quoted him.
Regarding the origin of Xmas you can hear a shiur on the subject by Rabbi Lawrence Kelemen on-line.